Gold-catalyzed addition of carbon nucleophiles to propargyl carboxylates

Organic Letters

Volumn 9, Issue 20, 2007, Pages 4021-4024

  Amijs, Catelijne H M ^a   López Carrillo, Verónica ^a   Echavarren, Antonio M ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35048842179     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701706d     Document Type: Article

References (37)

1. (a) Fürstner, A.; Davies, Y. W. Angew. Chem., Int. Ed. 2007, 46, 2-42.
2. (b) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395-403.
3. (c) Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750-2752.
4. (d) MarcoContelles, J.; Soriano, E. Chem.-Eur. J. 2007, 75, 1350-1357.
5. (e) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2006, 333-346.
6. (a) Mamane, V.; Grees, T.; Krause, H.; Fürtsner, A. J. Am. Chem. Soc. 2004, 726, 8654-8655.
7. (b) Fürstner, A.; Hanen, P. Chem. Commun. 2004, 2564-2547.
8. (c) Fürstner, A.; Hanen, P. Chem.-Eur. J. 2006, 72, 3006-3019.
9. (d) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. 2006, 45, 2901-2904.
10. (a) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 727, 5802-5809.
11. (b) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 727, 18002-18003.
12. (c) Zhang, L.; Wang, S. J. Am. Chem. Soc. 2006, 128, 1442-1443.
13. (d) Zhang, L. J. Am. Chem. Soc. 2005, 727, 16804-16805.
14. (e) Wang, S.; Zhang, L. Org. Lett. 2006, 8, 4585-4587.
15. (f) Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 8414-8415.
16. (g) Marion, N.; Diez-González, S.; de Frémont, P.; Noble, A. R.; Nolan, S. P. Angew. Chem., Int. Ed. 2006, 45, 3647-3650.
17. Structure 4 is more consistent with calculations: Lemière, G.; Gandon, V.; Cariou, K.; Fukuyama, T.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2007, 9, 2207-2209.
18. (a) Maineti, E.; Mouriès, V.; Fensterbank, L.; Malacria, M.; MarcoContelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132-2135.
19. (b) Cariou, K.; Maineti, E.; Fensterbank, L.; Malacria, M. Tetrahedron 2004, 60, 9745-9755.
20. (c) Harrak, Y.; Blasykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 726, 8656-8657.
21. (d) Bhanu Prasad, B. A.; Yoshimoto, F. K.; Sarpong, R. J. Am. Chem. Soc. 2005, 727, 12468-12469.
22. (a) Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505-8513.
23. (b) Miki, K.; Fujita, M.; Uemura, S.; Ohe, K. Org. Lett. 2006, 8, 1741-1743.
24. López, S.; Herrero-Gómez, E.; Pérez-Galán, P.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 6029-6032.
25. (a) Toullec, P. Y.; Genin, E.; Leseurre, L.; Genêt, J.-P.; Michelet, V. Angew. Chem., Int. Ed. 2006, 45, 7427-7430.
26. (b) Amijs, C H. M.; Ferrer, C.; Echavarren, A. M. Chem. Commun. 2007, 698-700.
27. 2SO leads to aldehydes in a process in which the sulfoxide attacks the carbene: Witham, C. A.; Mauleón, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 729, 5838-5839.
28. Endo, K.; Hatakeyama, T.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2007, 729, 5264-5271, and refs therein.
29. (a) Nieto-Oberhuber, C.; López, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 727, 6178-6179.
30. (b) de Fremont, P.; Scott, N. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 2411-2418.
31. (c) Porcel, S.; Echavarren, A. M. Angew. Chem., Int. Ed. 2007, 46, 2672-2676.
32. (d) López, S.; Herrero-Gómez, E.; Pérez- Galán, P.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem. Int. Ed. 2006, 45, 6029-6032.
33. Sanz, R.; Miguel, D.; Martinez, A.; Alvarez-Gutiérrez, J. M.; Rodriguez, F. Org. Lett. 2007, 9, 727-730.
34. See Supporting Information for details.
35. Georgy, M.; Boucard, V.; Campagne, J.-M. J. Am. Chem. Soc. 2005, 727, 14180-14181.
36. 1H NMR data for E- and Z-enol esters: Doucet, H.; Höfer, J.; Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1993, 850-851.
37. 1H NMR data for Z-enol esters: Doucet, H.; Martin-Vaca, B.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247-7255.